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【结 构 式】 
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【药物名称】SPI-339, NEO-339 【化学名称】4-[3-(4-Oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)propionamido]benzoic acid ethyl ester 【CA登记号】 【 分 子 式 】C20H22N2O4 【 分 子 量 】354.40934 |
【开发单位】Spectrum Pharmaceuticals (Originator) 【药理作用】Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
The reaction of 4-aminobenzoic acid ethyl ester (I) with acryloyl chloride (II) by means of TEA in dichloromethane gives the corresponding acrylamide (III), which is condensed with 4,5,6,7-tetrahydro-1H-indol-4-one (IV) by means of K2CO3 in hot DMF to yield NEO-339. (1,2)
| 【1】 Mohan, P.; Fick, D.B.; McKinley, L.K.; Prigaro, B.J.; Pfadenhauer, E.; Helton, D.; Search, design and discovery of NEO-339, a novel agent that increases attentional processes associated with cognition. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 249. |
| 【2】 Foreman, M.M.; Glasky, A.J.; Fick, D.B. (Spectrum Pharmaceuticals, Inc.); Synthesis and methods of use of tetrahydroisoindolone analogues and derivs.. EP 1383742; WO 0285856 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16498 | Benzocaine; ethyl 4-aminobenzoate | 94-09-7 | C9H11NO2 | 详情 | 详情 |
| (II) | 11577 | Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride | 814-68-6 | C3H3ClO | 详情 | 详情 |
| (III) | 64783 | ethyl 4-(acryloylamino)benzoate | C12H13NO3 | 详情 | 详情 | |
| (IV) | 64784 | ethyl 2-[2,3-dihydro-1,4-benzodioxin-5-yl(2-ethoxy-2-oxoethyl)amino]acetate | C16H21NO6 | 详情 | 详情 |
Extended Information